Potassium Carbonate → HCID 67528343, compound

HRID 1867548Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)#[N:12].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:11]#[N:12])[CH:18]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3 g (14.92 mmol) of 2-(4-bromophenyl)ethanol, 2.85 g (19.40 mmol) of 3-cyanophenylboronic acid, 5.15 g (37.30 mmol) of potassium carbonate, 4.81 g (14.92 mmol) of tetran-butylammonium bromide and 0.067 g (0.30 mmol) of palladium diacetate in 15 ml of water is heated at 100° C. under an argon atmosphere overnight. It is cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated. It is subsequently purified by chromatography on silica gel, eluting with a 70/30 then 50/50 mixture of cyclohexane and ethyl acetate, to give 2.90 g of product in the form of an oil, which is used as it is in the following step.

Workup

temperatureIt is cooled to ambient temperature
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over sodium sulphate
customevaporated
customIt is subsequently purified by chromatography on silica gel
washeluting with a 70/30
addition50/50 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record: ord-1f7465575227425e989c725bbea15770
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632850B2

Reaction notes

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